


Debt Repayment

by dementeddesires (lewdboy55)



Category: Dangan Ronpa: Trigger Happy Havoc
Genre: BDSM, F/M, Humiliation, Rope Bondage
Language: English
Status: Completed
Published: 2020-11-12
Updated: 2020-11-12
Packaged: 2021-03-10 05:41:42
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,179
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27519310
Author URL: https://archiveofourown.org/users/lewdboy55/pseuds/dementeddesires
Summary: Losing it all and being in debt to the Ultimate Gambler, this unlucky man goes through his first day as a servant to her as a form of debt repayment.
Relationships: Celestia Ludenberg/Original Male Character(s)
Kudos: 9





	Debt Repayment

I sat down in the comfortable limousine and looked down at the floor. The handcuffs felt tight and uncomfortable as I fiddled with them. “Don’t bother messing with them. It won’t get any looser than it already is.” A man dressed in a suit and tie mocked me. “Although I dunno if you’ll even listen. You are pretty fucking stupid after all.” Several of the other suited men laughed as I clenched my fists. The fucking bastards were right though. I had bet my debt over and over against my debtor on poker and again and again I lost. I had nearly won that last game. I had a straight flush, the second-best hand in poker, but she had a royal flush and utterly crushed me. She probably noticed then that my utter despair had taken over, and without a way to pay off the sum I was now being made to work for her until she believed my debt was cleared. I was essentially a slave until she felt by debt was payed, and anything she said I was going to have to do. 

“Why the hell did you even bet your debt again and again? That’ll just sink you deeper and deeper!” One of the men asked. “I thought that if I had won at least once with such a large debt, then it’ll be cleared. She can’t win all the games, right?” My answer caused the men to laugh harder. “I don’t get it, what the fuck is so funny?! Did she rig the fucking game?!” The laughter was immediately cut short by my accusation. “You really don’t know her then huh? Celestia Ludenberg. The greatest gambler to ever live. She’s a goddamn Ultimate you know. She ALWAYS wins her games.” I shook my head. “W-what? No, I was against-” One of the men interrupted me before I finished. “She’s banned from gambling at some places so she probably used an alias. Changed her looks and all.” The mood went a bit more somber. “We were just told you challenged her and lost. Jeez you really didn’t know your opponent? That’s just bad fuckin’ luck my man.” One of the men patted my back. I was as still stiff and on edge. Something felt weird about their sudden sympathy. “Still, pretty fucking stupid to do what you did even if it wasn’t her you were up against.” 

The rest of the ride was silent until we arrived at the elaborate mansion. I was forced out of my seat and nearly dragged along the entrance. As the two large, silver doors opened the men dragged me further in. My eyes darted around and I noticed that it looked more like an elaborate castle, with chandeliers that decorated the enormously high roof. There were several suited men walking around, looking busy and focused on their jobs. The men let me go, and as I began to stand one of them knocked me down on my knees and forced my head to the ground. “Stay like this. She will arrive shortly to meet you.” I felt one of the men unlock my handcuffs and put them away. A harsh whisper then crept to my ears. “If you run, she’ll make it so that your screams will reach the ears of no god, you cry of help muted until you are suffering for eternity. Understand?” I gulped and nodded slowly. The man patted my head and then left. I stayed in this kneeled, bowing position for what had felt like an eternity. Then, footsteps. 

I remained in the position, then I felt a foot press down on my head. I winced a bit, and she rubbed her foot as she pressed harder down. “Hmph, it appears you were compliant in arriving and without giving my servants too much trouble. Obedience will do you good, debtor.” I remembered that voice, its smugness and cockiness fueled an anger inside me that I must contain. It was the same woman I had lost to, her real name, etched forever in my mind, is Celestia Ludenberg. I swallowed my pride and replied. “Tha-” I felt her stomp on my head, causing me to scream in pain. There was a snap of a finger, and I felt a gag quickly get placed on my mouth as my breathing quickened, my eyes darting around and my head being held down as I tried to get up. “You must only speak when I give you permission! Learn that you are nothing but worthless trash!” She kicked my ribs and the gag muffled my pained response. She seemed satisfied with that and returned with her foot on my head, “Miguel. Antonio. Change him into a proper attire. As for his name...I think Vincent is suitable.” Her laugh filled the room, and once she left the men picked me up and dragged me away. They removed the gag, letting me get some fresh air. “Mistress Ludenberg likes you.” One of the men said. “What the fuck makes you think that?” I groaned. “She didn’t whip you.” The other replied. 

I was dragged along to a dressing room, where the men began to undress me. “I-I’m more than capable of changing clothes myself!” I assured them. The two nodded and took a step back. “Apologies, Vincent. We’re in charge of dressing her so it’s a bit of a habit. I’m Miguel and this is Antonio so you don’t get us confused.” Miguel bowed, followed by Antonio. The two looked...pretty similar. Tanned skin, decently tall, somewhat muscular. The kind you’d get jealous of if you aren’t already a good-looking guy. “So, you two brothers?” I asked as I took off my shirt. The two chuckled. “Twins actually!” They said in unison. Antonio brought me a butler’s outfit, with the suit, tie, whole shebang. There was something weird though. “Why do I need to wear this collar?” I asked. It looked similar to one you would put on a dog. The collar had no leash, but the word “Vincent” was etched to the side, along with “Property of Mistress Ludenberg.” Miguel observes the collar a bit. “Ah, are you not fond of the color? Do you prefer another? Not a fan of black?” He asked. I shook my head. “N-no it’s why do I need to wear it at all? Besides my name isn't even Vincent. Its-” Antonio covers my mouth. “Shh. Do not speak your real name. Your new name is Vincent, and that is final. She is our Mistress, and we serve her. Be glad she called you a name of value. She could have called you something worse. As for the collar, all new servants are required to wear one. Once you have earned her respect then you may get it removed.” I nodded slowly with wide eyes as I stared into Antonio’s fierce gaze. He slowly moved his hand away and began to dress myself in the awkward silence. “So... what jobs will I need to do?” I asked. The men shrugged. “It varies. We have been here for a long time, but are not the first servants. Our job has always been to dress Mistress Ludenberg and assist new servants. I do think though you may be placed on kitchen duty. Hope you can cook!” Miguel smiled and patted my back. 

Once I was dressed and my collar on, nice and snug, I was sent to meet the head butler. It was an older gentleman sitting in front of a large monitor, observing anything and everything that was happening. “Ah, the new servant Vincent.” The man greeted me without even turning around. “Antonio. Miguel. You two may take your breaks now. Head to Mistress Ludenberg’s location to inform her of your break. She is currently in the indoor pool.” I turned around and the twins seemed pretty happy, with wide smiles. “Thank you, Sir Alexander.” The two bowed and spoke in unison, then quickly left. “As for you, Vincent. Mistress Ludenberg has requested you to specifically handle the cleaning of her room. Take a tablet to your left on your way out, it shall provide a map of the mansion as well as your required tasks for the day. Do not mess up, for I am always watching.” Sir Alexander spoke those ominous words and I quickly grabbed a tablet and left. 

I arrived at her room with several cleaning supplies I got from what the tablet called the “Janitor’s room” and was in awe at the sheer size of her bedroom. That single room was larger than any apartment I had ever been inside, and her bed looked as if someone combined three king sized beds together! “People would sell their soul for a fraction of this luxury...” I mumbled to myself. The room itself was very gothic, fitting for how she dressed and behaved, judging from the clothes scattered along the floor. If gothic princess was a style, this room would encapsulate that entirely. That probably is a style though, and I might just be uncultured, Regardless, I had chores to do. 

I was surprised at how much of a mess she left her room in, but then again, she has people to clean rooms for her so she might as well use them. I made the bed, placed her clothes back on hangers and in her walk-in closet, in the spots instructed by the tablet. Some drawers were open so I closed them, and as I was collecting trash the door slowly opened. “It seems you are slow to work as your brain is slow to think, Servant Vincent.” Mistress Ludenberg’s way of talking down to everyone was something that I got sick of the moment she opened her mouth. I said nothing, not wanting to piss her off and just kept collecting the trash, getting on my knees to check under the bed. I felt her foot press on my head again. “It seems you actually learned not to speak unless spoken to. I give you the privilege to thank me. That is my reward to you, Servant Vincent,” I could feel a smirk rise from her lips, and I held back a snide remark. “Thank you, Mistress Ludenberg.” I replied, but it wasn’t how she wanted it. She pressed her foot down hard until my head hit the floor. I was glad it was a carpet floor this time. “Repeat it, with meaning and want. I am giving you a gift, you disgusting pig. Now thank me properly, open that disgusting mouth of yours properly and thank me as loud as you can!” She had a sadistic laugh once she finished uttering those words. I then gave her a loud and hearty “THANK YOU MISTRESS LUDENBERG!” 

“Again!” She shouted, pressing harder on my head. I would repeat my thank you and she would press harder, until my voice began to crack. She slowly moved her foot away. “There. That is a proper thank you to your Mistress.” I slowly stood up and coughed, my throat feeling sore. I noticed her clothes were very different from when I saw her. She looked like a gothic princess with skin as pale as can be. I would ask what part of Europe she is from, but she spoke before I could make the mistake of speaking. “Slow but diligent. I am impressed, you can at least do your assigned task well.” She sat down in the bed. “Finish tossing out your collected trash and return here.” She snapped her fingers to end that sentence. I wasn’t finished with my tasks, but I wasn’t about to correct her. I bowed and left to throw out the trash in her room. 

Once I came back to the room, I noticed the door was locked. Curiously, I knocked. I got a response. “Unless it is an emergency, someone is dying, or Servant Vincent I suggest you leave immediately!” I then replied, saying it was Servant Vincent. I heard the door unlock and I made my way inside. I noticed she had a small box in her lap, along with a strange smile across her lips. “Take a seat, Servant Vincent.” Naturally I sat next to her, but she kicked me off the bed. “On the floor! It’s where you belong!” She snickered and I slowly sat up, getting pretty fed up with this shit but having no choice but to put up with it. “Servant Vincent, I give you the permission to answer questions with honesty. Now, no need to thank me. Simply kiss my foot as thanks.” She raised her foot near my lips. I glanced up at her, giving a bit of a weird look as I pecked her foot. She seemed satisfied and patted my head with her foot. “You’re learning better than I thought! It seems your small brain can grasp something.” She moved her foot away from my head and took out some black, leathery rope. “Question one, do you have experience with rope?” 

I shook my head no. “I never really used rope for anything. Sorry, but I can’t really be a cowboy or whatever it is that requires rope.” I braced myself to get hit, but instead she just sighed. “Understandable. You don’t seem the type. Question two, have you ever had a girlfriend?” I looked up at her with a slight blush. She tilted her head, then covered her mouth with her hand. Her smirk was still visible on the edges of her lips. “You never had a girlfriend, have you?” I slowly nodded my head. “Y-yeah. It’s pathetic I know...” I sighed. She gently patted my head with her foot, “There, there my little servant. I just have one last question. Are you a virgin?” She asked with a teasing smirk. I looked up at her, my face red. “W-why the hell do you wanna know that?!” I asked. She lowered her foot and pressed down on my crotch, then grabbed my chin and forced me to look into her eyes. “Because you are indebted to me, and I want you to know I will take all I can from you. That includes your virginity, and any semblance of you thinking you have any ownership of your body. You are mine, from your head to your toes. This, included.” She pressed her foot harder down on my crotch so I understood what ‘this’ meant. I grunted and before I could speak, she covered my mouth with her other hand. “Don’t worry, my little servant. You will enjoy it. Everyone does.” 

My eyes were wide, and my heart was racing. I was confused, a bit scared as well. As soon as she let go of my mouth, she brought her lips to mine and kissed me deeply, holding my head to her lips. I felt her press even harder on my crotch as she pulled her lips away. “Kiss me back, or do you like this?” She moved her foot up and down my crotch, feeling where my erection was. I was hard and stiff by her stimulation, panting softly as she moved her foot. “Are you enjoying this punishment? Is my foot all that it takes to get you aroused, you disgusting pervert?” She smirked and kept going, my panting only getting heavier and deeper. She began to move her foot away once my bulge was particularly noticeable. “If you leave this room before we finish, I’ll make your life a living hell. Understand?” I nodded, trying to regain some composure. 

I was ordered to strip, and do so slowly. I began to take off my suit, then my tie and unbutton my shirt. She seemed to be a bit disappointed with my lack of a muscular body, but glanced down looking at my erection with more interest. I undid and pulled down my pants, and she spoke up. “Now, I want you to do this as slow as possible. I want to have either a good laugh or welcome surprise.” She had a sadistic grin, and I hoped I wasn’t in for more humiliation. I ever so slowly pulled down my boxers, revealing my shaft to her ever so slowly until my full erection was in view. I caught her licking her lips with a strange smirk. “Not small, but not the biggest. I think it can satisfy me. If not, then I’ll bend you over as punishment, my servant.” I was sure as fuck not looking to get pegged, so I hoped all those hours watching porn would teach me something on how to please a woman. She then pulled out a blindfold and put it on me. “Depending how well you do, you might earn the right to see me in all my beauty. For now, lay down on the bed, my servant.” She whispered. 

I stood up and began to lie face up on the bed with Mistress Ludenberg’s help, and I felt her tie my hands above my head, along with my legs being bound together by the rope. I gulped as thoughts began to race though my mind, and I felt myself get a bit too excited. “Oho? I noticed it twitched a bit! You really are a disgusting pervert, aren’t you my little servant?” She sneered. As I opened my mouth to call her a hypocrite, she placed a gag on me and kissed my head. “You are so easily falling for my traps. Such an imbecile, I think at this point you enjoy it. Well, according to your friend, you’re craving it.” I felt her slide her hand up my thighs and stroke my erection slowly, her thumb rubbing my tip as she stroked upward. My soft moans were muffled by the gag, and I focused my heavy breathing though my nose. I squirmed a bit as she kept going, and she laughed at my struggle. “Careful now, my servant. If you break those ropes, Ill break your filthy cock.” She squeezed my erection hard and I inhaled sharply. I fought against squirming more and she slowly let go. “Good, now stay nice and still for me.” 

She moved her hand away and I felt her put something on my erection. I assumed it was a condom and what she said once it was on made it clear it was. “I won’t have the unfortunate opportunity of bearing your children. Last thing the world needs is more of you.” She spat out, and I just lay there and took her insults. Not like I could even say or do anything in protest. She was silent for some time, and I suddenly felt her get on top of me. She lowered her head just next to my ear and whispered softly. “I will take everything from you, starting with your virginity. Be thankful.” She bit my ear softly, and then I felt her grab my erection and guide it inside her. She moved her hips down slowly, gasping softly as she did. She was tight, and I felt her clench around my dick as I tried to moan out. I took heavier and deeper breaths through my nose, with muffled whines trying to escape my lips as she moved her hips up and down. 

“You feel bigger than you look, and your thickness is certainly welcome, servant~.” Mistress Ludenberg whispered in my ear with a sultry tone, licking my cheek as she moved her hips faster, slamming them down to my thighs as she wrapped her arms tight around me, clawing my back in passion. I tried to let out more struggled moans as drool began to drip from the sides of my lips. She noticed and spat on my head, then started digging her nails deeper in. “You’re such a filthy mess, Vincent. Exactly how I l love my men. Shivering, drooling, lusting, and forever knowing their place beneath me. You disgust me, you’re nothing but a piece of meat for me to ride.” She laughed sadistically. She slowed down a bit, moving her hips in a circle as she took my entire erection inside her. I felt my mind slowly turn blank, the pleasure getting to my head as I whimpered and moaned under her dominance. The pain I felt from her clawing at my back turned into pleasure, and I felt I was getting closer and closer to climaxing. 

Just before I could, I felt her suddenly get off of me, and take off my drool-covered gag. As I gasped for air, I began to beg helplessly. “W-why? Please Mistress Ludenberg please I am so close!” She simply placed her foot on my chest, and gave me a cruel response. “I know. That’s why I stopped. You think I will give you the right to spill out your seed? Not until your Mistress does first.” Before I could continue my pleas, I felt her thighs squeezed between my head and something touch my lips. “Use your tongue. Afterwards...I might give you that release.” I nodded quickly and softly kissed her entrance, slowly licking it and inserting my tongue. 

Her hands reached into my hair as she tugged on it hard. “Move that tongue deep inside me and make me cum all over your disgusting face, pig!” She tugged harder on my hair, and I let out a whimper as I moved my tongue faster inside her, wiggling it and licking up her juices. I could hear her moaning louder, inspiring me to press my lips closer against her and reach deeper in. I felt her move her hips and start to ride my tongue, pulling my head closer to her as she filled the room with her moans. She moved her hips faster and faster, while I continued to maneuver my tongue inside her until she squeezed my head with her thighs and I felt her clench around my tongue. She let out one final moan and my face was covered in her climax. 

She took deep, heavy breaths as she sat on top of me, my head between her thighs and her hands gripping my hair tight. After what felt like thirty minutes, she got off me, and I noticed she got off the bed. I took a few deep breaths of fresh air and spoke. “M-mistress Ludenberg w-what about me?” I asked in a whiny tone. She didn’t answer, but instead took off my blindfold and I saw that she was dressed. “I will give you that release, after all you did please me with your tongue. In fact, I will even give you a special reward for it. She reached her hand down and slowly took of the condom, tossing it aside. She began to kiss down my chest, until she was face to face with my erection, and began to lick from my balls to the tip, kissing my tip tenderly. “Rejoice, servant. You get to be one of the lucky few who are worthy of my lips.” 

“Th-thank you Mistress Ludenberg!” I spoke, and she giggled as a response. “Stay quiet, servant. I only want to hear your desperate moans. She licked her lips and slowly wrapped her lips around my tip, sucking tenderly on it as her tongue moved in circles around it. I let out a sharp gasp and she slowly made her way down my shaft, her hand caressing my legs as she continued to suck. I began to moan louder and louder as I felt myself get lost in the lust and pleasure. “M-more please! Keep going Mistress Ludenberg please don’t stop!” I begged, and she slowly moved her lips up and made popping noise as she moved her mouth out of my erection. “You’re so cute when you beg, do it more.” She ordered, rubbing my shaft against her chin, kissing my shaft and licking it. “P-please Mistress Ludenberg please keep sucking on my dick! I need it I need your mouth and I need you! I want you so bad please I’m getting closer and closer! I want to cum Mistress please!” I continued to beg as if my life depended on it, panting and whining as she kept on licking my shaft. 

“How about this...if you can last one minute while I deepthroat you, I will let you order me to do one thing.” She grinned smugly, then set a timer on my tablet. “If you fail, then I’ll have your new uniform be nothing but a tattoo across your back that says “Property of Celestia Ludenberg”. You will be my bitch, made to walk on all fours and bark. I will even have you go out for walks, and show you the true meaning of humiliation. Oh, and if you decline, I’ll make you my dog anyways. So, you accept?” Of the two options I decided to go with the one that gave me hope, and I accepted with a shaky breath. “Good answer. Now, you better not cum, unless you want to be my adorable little mutt.” She smirked and immediately moved her lips all the way down to my shaft and started the timer. 

I immediately moved my hips up, moaning out at the sudden rush of pleasure as I felt her gag and deepthroat my cock. I took heavy breaths and tried to hold it all in as she bobbed her head, her tongue moving around my shaft. I glanced at the timer and fifteen seconds had passed. She gagged loudly and bobbed faster, choking and throating me like a professional. My eyes had rolled to the back of my head and I felt like I had ascended to heaven. Pleasure rushed through my body as I tried my best to hold back from finishing in her mouth. I felt her hand cusp and play with my balls a she throated me and it was enough to drive me over the edge. I let out a loud moan and climaxed inside her mouth, shivering and passing out, with the last thing I hear is her swallowing my seed. 

I awoke on the floor in her room, with the bounds undone on my arms and legs. I stood up and noticed on the table a camera with a note on it. I approached and read the note. “You passed out and I was forced to swallow your disgusting seed. I recorded the ending of our session with a timer in view, so you can see for yourself the results.” It was signed ‘Mistress Ludenberg’ and I immediately began to play it. The video was longer than one minute so there was no way to tell right off the bat if I made it or not. It began with her giving me a regular blowjob, so I fast-forwarded until the deepthroat started. I checked the timer and I had two minutes left. Strange, but I watched. I noticed that the moment I moaned before passing out, it was exactly one second after the minute mark. “I-I did it...yes! Fucking yes! I can order her to remove my debt!” I grinned. I then saw her approach the camera, open her mouth to reveal my seed and then swallow it all in one gulp. She then opened it again and licked her lips. “I’ll be waiting for your order, Servant Vincent. Meet me in the pool.” With a wink, the recording stopped. I decided to take the camera and keep it for myself, then rushed to the pool once I dressed myself. 

After some time of getting a bit lost, I found Mistress Ludenberg. She was in the indoor pool, wearing a black bikini and reading a book. “Mistress Ludenberg, I have arrived.” I spoke, and she put her book away with a smirk. “Good. Now, what is the one thing you wish to order me to do?” She asked. I opened my mouth but then closed it. I thought for a bit what to ask for. I could just wish away my own debt, but that still leaves me in a shitty position once I leave. I still have no money to pay for rent, my parents are dead so there goes living with them. I don’t have any friends that are willing to help me out as well. “What is taking so long?” Mistress Ludenberg asked, a bit confused and impatient. She was even more confused as a smug grin was creeping on my mind. 

“I order you to expunge my debt, and rehire me as a regular butler, with a pay of a thousand dollars an hour. Two week vacations a year, and sex at least once a week. Unless you are sick or something happens.” I gave my demands and she laughed, clapping her hands. Now it was my turn to get confused. “I appear to have misjudged you, my dear servant Vincent! I assumed you would just expunge your debt or ask me to perform some lewd, depraved sexual act! Instead, you asked for something a lot more interesting. Tell me, why not simply ask for your debt expunged, or ownership of the mansion, or some other thing?” 

I rubbed the back of my head and explained that I no longer had family, or friends to return to if I was cleared of debt. I still would have no money and end up homeless. I explained if I simply asked for money, you would take it and I would still be in debt. If I asked for ownership of the manor, you would take it back as I still have your debt and I would end up in the same spot if I asked for my debt to be expunged. I was fucked in all directions and had only one option. “It was tempting to ask to fuck your ass, but that would be stupid, and I would really gain nothing. So... might as well make the best of it.” Mistress Ludenberg clapped her hands, with a warm smile on her face that made me feel unsettled. “Good. Very, very good. I accept the conditions, however about that last part, I wish to come to some sort of compromise.” I was surprised she was so readily accepting of this deal, and the only issue was the last part. Then again, it was basically guaranteed sex. “What's there to change?” I asked. She smirked. “Make it every single day. Oh, and I hope you don’t mind if other servants join. I have a similar deal with the ones who don’t wear collars. After all, the men I enjoy are ones I break easily. The ones that I love the most are ones who can put me in my place, especially with all their pent-up frustrations about me.” She approached me and licked my neck, then whispered softly in my ear. “Do we have a deal?” She then reached her hands up and freed me of my collar. I reached my hands down and grabbed her ass. “We do. Now bend over, I think I’m taking my break early.”


End file.
